Detection and Elimination of Product Inhibition from the Asymmetric Catalytic Hydrogenation of Enamines
- 29 September 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 7 (22) , 4935-4938
- https://doi.org/10.1021/ol051862d
Abstract
The catalytic asymmetric hydrogenation of enamine amides and esters with catalyst Rh-1a, prepared from ferrocenyl based ligand 1a or 1b and [(COD)RhCl]2, has been shown through kinetic studies to suffer from product inhibition. Enamine ester substrates have also been shown to be incompatible with the amine products of the reaction in methanol. In situ protection of the amine products with di-tert-butyl dicarbonate eliminates functional group incompatibility of ester substrates and eliminates product inhibition in the reaction.Keywords
This publication has 6 references indexed in Scilit:
- Highly Efficient Synthesis of β-Amino Acid Derivatives via Asymmetric Hydrogenation of Unprotected EnaminesJournal of the American Chemical Society, 2004
- Recent Developments in the Catalytic Asymmetric Synthesis of α‐ and β‐Amino AcidsAngewandte Chemie International Edition in English, 2003
- Amine Products and Catalyst Poisoning in the Homogeneous H2 Hydrogenation of Imines Catalyzed by the [Rh(COD)(PPh3)2]PF6 PrecursorOrganometallics, 2003
- Protective Groups in Organic SynthesisPublished by Wiley ,1999
- [HC(py)3W(NO)2(CO)](SbF6)2 as a Lewis acid precursor in additions of silylated C-nucleophiles to carbonyl compoundsTetrahedron Letters, 1993
- Structural and solvent effects evaluated from acidities measured in dimethyl sulfoxide and in the gas phaseAccounts of Chemical Research, 1988